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Elfen Lied is the saddest anime I've ever seen. The combination of endlessly cute characters and merciless violence, suffering and hate was just too much for me to bear. I found myself crying towards the end.

Another honorable mention for the title is end of evangelion, it was a brutal ending to the series, especially because I didn't see any of the brutality coming.

Anyway, Mahoromatic was the most depressing show I have ever seen, by far. Saikano? Kimi ga Nozomu Eien? Pah, those titles are nothing compared with Mahoromatic's descent from light-hearted ecchi comedy to heart-piercing, utterly gloomy tragedy. The ending was shockingly terrible, and the lowest point of the entire series in my view, which only cemeted the series in my history as the saddest I've ever seen. It has no peer.

its the first n only anime i had to stop watching afther a few eps couse i coulnt emotionally handle it anymore.
that anime got me so down n sad that ive been crieng myself to sleep for like a week because it got stuck in my head.....

its the most painfull anime ive ever seen,
even though ive only saw a few eps.... ^^....

....mits

ps. i also remember FMA making me cry alot but,
that wasent as painfull to watch as the sadness & Sorrow of Kimi ga nozomu eien

I've seen quite a few animes since my last post, so I'll add a few. Though it seems a lot of people have already mentioned these, so it might be redundant. Nevertheless!

Air. Both the series and the movie were flawless works of art in my opinion, and the level of emotional involvement was very high. Misuzu was absolutely adorable (Nihaha), which made the whole anime all the more depressing. I can't help but smile when I think of her,

Spoiler for Air spoilers:

though the feeling is bittersweet. Some of the scenes are just heartbreaking, I especially recall the one where she comes walking out of the school and tells the crow that she couldn't find anyone to play with this summer either. And the ending is of course utterly depressing as well.

Hanbun no Tsuki ga Noboru Sora. I'm amazed they managed to put so much emotion, feeling and story into just 6 episodes. The series was less sad than Air, but it was still quitel an emotionally draining experience.

Spoiler for Hanbun no Tsuki ga Noboru Sora spoilers:

The ending was bittersweet, at least they'll hopefully spend a good amount of time together before she passes on. If she would have just died during the operation, as I feared she would, I would have just crumbled, emotionally.